“Should I Cold Email My Brother’s Best Friend?”

I am 25, single, and have a dilemma: I’m interested in my brother’s best friend, “Peter.” In my list of qualities I look for in a guy, he meets every one: he’s 32 (I’ve always seen myself with someone 6-8 years older), educated, goal-oriented, Catholic, good-looking, etc. I’ve always been attracted to him. He’s in medical school nine hours away in my home state and has been friends with my brother since grade school. Fast-forward to 2009 when I was visiting my sister and complaining to her about my dating troubles. She nonchalantly suggested that I get Peter’s e-mail from my brother and e-mail him. She said I ask him how medical school is, how he is, and just strike up a friendship. I brushed off her suggestion … until now: I am starting to seriously consider it. I’ve dated a lot in my city but haven’t found what I’m looking for. I’m also older now and feel ready for a relationship (which I realize can be hard to establish nine hours away, but could be done). It occurred to me I could find his school e-mail on his school’s directory, which I did, so I wouldn’t have to involve my brother by asking for Peter’s personal e-mail (although Peter may tell my brother if he receives an e-mail from me – this is the brother that I’m closest to, by the way). When I was home in August, I asked my brother if Peter was dating anyone and he said no.

I’m leaving my dating options open in my city, but I thought I’d try this too and see what happens. I don’t plan on moving back to my home state and it’s rare that I’ve been home when Peter is visiting my brother, so I’m not quite sure how else Peter and I would get together. The last time I saw Peter was two years ago. I also figured that cold-emailing him is just like online dating, but in this situation I know him and have met him before. Peter has always been in the back of my mind as a possibility, so I was thinking, what if?

What do you think about my e-mailing him? Is it a bad idea? On the one hand, I don’t think it is and there’s always the possibility it could turn into something, but on the other hand, Peter could think it is really out of the blue (which it is), say something to my brother and then I’d have to have an awkward conversation with my brother. If you don’t think it’s a bad idea, do you have any advice for what to write in the first e-mail? — Cold E-mail

It’s not necessarily a bad idea, but going about it the way you’re planning to does pose some risks and lots of potential awkwardness. First of all, cold-emailing someone you haven’t seen in two years, whom you’ve never emailed before, whose email address you tracked down on a school directory, and with no excuse at all isn’t quite like online dating. Not at all really. People on a dating site are actively seeking someone to date; for the most part, they’re welcoming emails from potential matches. At the very least, they’re prepared for them and have put themselves in a position to receive them. That’s not the case with Peter. He doesn’t know you have his email address, he hasn’t seen you in two years, he’s not expecting to hear from you, and, frankly, might wonder why, all of a sudden, you’re sending him an email asking how’s doing. You’d be better off if you had some excuse to contact him — like brainstorming a gift for your brother, asking a specific question about medical school for a “friend” who’s considering applying, or seeking advice on a topic he knows something about (for example, if he’s an extensive traveler, you might ask him for vacation suggestions). The point is, you need some excuse to contact him besides just wanting to say ‘hi’ when you’ve never really said ‘hi’ to him to outside your brother’s presence and you haven’t seen him in two years.

And speaking of your brother, it’s a pretty risky move to reach out to his best friend behind his back. It makes what you’re doing seem suspicious — the whole looking up Peter’s school email address in his school directory instead of just asking your brother for his personal email begs the question: “What are you trying to hide?” Why not just ask you brother for it? Unless you think he wouldn’t approve, in which case, you might want to talk to him about your plan before creating potential drama between you. It’s a good idea to give him a head’s up even if you’ve already decided you’re going to go for it whether you’ve got his blessing or not. And for all you know, he would approve and he may have some helpful insight for you. Maybe he can provide you a good excuse to reach out to Peter or advise you on how to compose an email that won’t seem completely random. If he’s a really nice brother, he might even play matchmaker and put in a good word for you with Peter. Hey, anything’s possible, right?

*If you have a relationship/dating question I can help answer, send me your letters at [email protected] and be sure to follow me on Twitter.

My brother and I are super close, and while I don’t think he’d mind me dating one of his close friends if I happened to be interested in one of them, I do think he’d mind me going about it behind his back. Even though it might seem awkward, think about how much MORE awkward it would be if a relationship worked out and you ended up having to tell your brother about it months down the line. I’d casually mention to him that you find Peter cute – or what have you – and ask your brother directly for his e-mail. If he’s anything like my lil’ bro (ie, generally pretty awesome), he won’t make a big deal out of it.

I agree with Wendy that a practical ‘reason’ is needed to not tthrow Peter for ‘a weird loop. On the other hand, you run the risk of getting his advice/response, and him considering the matter closed, the ‘question’ addressed. This is another reason you ought to let yr bro in on it, so that he can help you, if he wants to, approach Peter in a non-threatening, non-random way that—key!—actually opens up additional communication. Also, yr brother might be able to suggest a better way for you two to get back in touch. Maybe he can talk you up to Peter and arrange for you two to be visiting him or be in town at the same time and all hang out together for drinks or something. Casual, and super easy to reconnect after 2 yrs with yr brother there as a common link.

Yeah, yikes, I wouldn’t do it unless you have a really really good excuse that you can play off to look natural. It doesn’t seem likely, but if you’re able to do that, and he emails back, and best case scenario you establish a friendship, I would NOT actively pursue him and ask him out. If he likes you, let him do the asking. Otherwise you set yourself up to be either rejected, or treated casually and not the way you’d want.

But a larger point is, why are you trying to establish a relationship with a guy who lives 9 hours away and is in medical school? It sounds like you’ve built this guy up in your head and are starting to fixate on him like he’s your “meant to be” solution to an unsatisfactory run of dating in your home town. I feel like you’re building this up in your head because it makes you feel better about the future. It has very little chance of going anywhere, and even if it did, would you really want to date a guy who lives 9 hours away and is that busy? I don’t think it would give you what you’re looking for.

Have you really done all you can do to date successfully in your hometown? Do you have a good online profile? Maybe have Wendy take a look at it! I just think you’ll be a lot happier if you meet a guy who lives near you, really likes you, and is available / has time for you. That doesn’t mean you can’t give it a shot with “Peter” by emailing under a good pretext, I just don’t think it’s likely to go anywhere and you’ll be disappointed.

Totally agree to your larger point. I did this myself when a good friend of mine left for military training. While he was away I built him up in my head as this new, older, more mature sailor with whom it was meant to be. We spent a few months long-distance to start, and he luckily (?) got stationed near my home and we started dating for real. Except it was nothing like it was in my head and I ended it about a month later. Wendy is right, let fate take its course.

Thank you for touching on the larger issue I neglected. It doesn’t make sense to aim for a relationship with a guy who lives nine hours away and is in medical school. LW, you’re betting off sticking with guys closer to home. If things are meant to be between you and Peter, fate will intervene at some point.

I agree, it really is a lot to think about, and this LW needs to really think about if she wants to go into this knowing it is going to be a LDR, with a lot more variables than most. She said she doesn’t ever plan on moving back to her home town so if this guy gets offered a job at the hospital where he is going to school it definitely isn’t going to work, and then she has to think that there is a chance this guy is going to move once he does his residency, and again when he goes into his specialty, or a fellowship. I think there is a lot to think about before the LW contacts her brothers best friend.

TOTALLY agree. The first thing I thought of when reading this letter is that this LW has built up a fantasy with this guy in her head. Why on earth, if you don’t plan on moving, would you want to get involved with someone who is 9 hours away?? Plus, as soon as he’s finished with school, he’ll have to go through the match and will be TOLD where he has to go for (depending on which residency program he’s in) at LEAST 3 years. Then if he wants to do a fellowship? He has to go through the match AGAIN! Depending on what he wants to go when all is said and done, he could be moving all over the country for years. I have a good friend whose husband has been out of medical school for TEN years and is still doing fellowships. They’ve moved like four or five times. LW, please think long and hard before starting something up with this guy. And as Wendy said, who knows, maybe fate will intervene and the guy will end up in a residency program closer to your city. But until then, I’d keep looking closer to home.

Agree! But not in a condescending way. Hey, we ALL have had that guy that we build up (the one that got away) and I think its perfectly natural and can even be comforting at times when being single feels especially crappy. It’s comforting to think there is that one “what if” guy out there. That somewhat ill-fated crush.

I don’t think there is any danger in reaching out and establishing some communication, maybe even a flirtation, but I agree to keep the focus at home where a more promising connection is likely to come. It just takes TIME to find a good connection. Stick with and take breaks as needed. He’s out there and I bet he’s closer than you think!

Is he on FB? You might do better to friend him on FB–it’s not at all odd there to get a friend request from someone you haven’t seen in years and are connected to by several degrees of Kevin Bacon–and then you could gradually re-get to know him (and also conveniently see if he’s obtained a girlfriend recently).

Though I worry that you may get your expectations up too high, if you’ve been thinking about him for two years. I think it’s good that you’re leaving your options open. It may be that you won’t click.

I was going to say this too…. just friend him on FB. You could casually write on his wall and be like “Hey, long time no see, how is med school treating you?” and see if he responds at all. Just strike up a casual friendship over FB, and if you’re really interested, make a point to seeing him next time you go home (like at Thanksgiving) and just see if there is any chemistry between you in person.

So true about the expectations. I mean the LW is clearly thinking about ways to sustain a relationship and she hasn’t even exchanged casual greetings with this guy in TWO years. For all she knows this guy hasn’t even given her a thought in all that time, and even if he has thought about her it was probably as his friends little sister.

I just have visions of them exchanging a couple of emails and then she freaks out with a response like “I think you need to move near me because the school districts are much better and I have already put down the deposit for Little Jr’s daycare.”

It would be smart for her to make sure she plays this calm and cool otherwise she is going to come across crazy and make sure to give him lots of time to possibly consider her as a potential love interest.

While I was reading this letter I kept thinking about that episode where Patti plays matchmaker to the self help gurus. And the one guy has this neurotically long list of non-negotiables in a partner (he’s also super creepy and gives the woman a pedicure and facial on the first date, but I digress!). I agree that a course of action is important if you’re actively looking for a partner, but there’s something clinical about the letter that made me feel she’s setting herself up for failure here. Like he meets criteria A B C D, etc. therefore a dating scenario must be executed. It was just a little weird to me.

And on another note- I love/hate Patti Stanger. My boyfriend and I have two reality show guilty pleasures: Millionaire Matchmaker and Ice Loves Coco (I know… no explanation for that lol).

Just be careful not to expect too much if you do use the Facebook approach. A guy living two US states away from me, who I’d met at a friend’s wedding three years ago but hadn’t spoken to since, made me his female “Peter” and contacted me out of the blue on Facebook. We were already Facebook friends, but the reason he gave for contacting me was kind of strange, and he never once directly said “dating,” so I felt weirder out from the get-go. The whole conversation felt unnatural – I was wondering why he was going for me when we both said we don’t plan to move, and there definitely should be plenty of women where he is.

To make matters worse, he said some borderline creepy (suggestive?) things and the whole conversation felt stiff and awkward. When I came clean and told him I was confused by his motives and not having fun, he got outsized hurt and promptly cut me off *and* blocked me on Facebook! He had expected a far warmer reaction and was shocked that I was both confused and uncomfortable with his approach.

So basically, Peter might react the same way – “Who’s this? Why is she contacting me? If she’s into me, why is she not forthcoming about it/asking her brother? What does she want knowing that we’ll never live in the same place? And aren’t there lots of guys where she is that she can date?” Since Facebook is not a dating site, it can turn out just as awkward as a cold call email to his school address for the same reasons. LW can Facebook him if she wants, but she should either try to meet him in person ASAP or not get her hopes up.

Yes this exactly! I wondered this too. I would be weirded out by a random email, but not if she were to send me a friend request and say something like “Wow, Peter, haven’t see you in forever! How’s everything?”

I have to ask, do you even *like* Peter? I mean, in a romantic way? In your whole letter, you never mention being attracted to him. I kept expecting to read that you’d had an enormous adolescent crush on him, that you feel a spark of excitement when you see him, that he’s your dream guy, etc. But all I can gather is that he is available and looks good on paper.

I think you need to ask yourself what your motives are. If all you want is a boyfriend, and there is no fundamental longing or attraction for Peter, I’d say you should pass. I mean, you haven’t seen him in two years, he’s in school in a different state, he’s your brother’s friend, etc. There are just so many obstacles to starting a relationship. If you want a “successful” boyfriend, I’m sure there is a medical school with single guys closer to your home!

It just seems strange to me – and frankly, a little desperate – that you would reach out to Peter just because you know he is a single. How are you guys even going to date? On Skype? Long distance is no way to START a relationship, especially when you haven’t already been hometown friends. Yes, Peter will think it’s weird that you’re emailing him. And unless he’s had an undying crush on you, I doubt he’ll think it’s worth the time, effort, and potential awkwardness around your brother to start something with you. I mean, just because your dating situation has held you to this point, it doesn’t mean that he is experiencing the same lack of options that would lead to a LDR with a girl in another state, whom he hasn’t seen in two years, and whom he knows only as his friend’s sis.

Just FYI, I edited out the lines (and have not put them back in): “In my list of qualities I look for in a guy, he meets every one: he’s 32 (I’ve always seen myself with someone 6-8 years older), educated, goal-oriented, Catholic, good-looking, etc. I’ve always been attracted to him.”

It’s clarifies things a little bit, but still– she’s rattling off qualities from a “list” she has in her head about what constitutes a good guy. The impression I’m getting is that she’s a very goal-oriented person herself, and her sights are now set on Peter after some disappointing dating experiences. Instead of the typical “I can’t find a good guy, what do I dooooooooo” letter, this LW has already supplanted Peter as the solution to her problems & just wants advice on how to snag him.

The solution is obvious, really. Approximately 83% of single women meet their life partners at weddings. So, . . . you just convince your brother to arrange a sham wedding to a model you’ve hired for the occasion. Peter is naturally asked to be the best man and you, fortuitously, just happen to be the maid of honor. As per the plot line of every romantic comedy ever written, you and Peter fall madly in love (although only after overcoming several intervening hardships that allow Peter to prove his ardor towards you). Your brother and the model’s marriage is revealed to be a sham. However, Peter has already proposed, and in an ironic twist of fate, your brother and the model fall in love for real this time as they both attend your wedding and everyone lives HEA. Got it?

Or, you could simply get off your duff and *call him* (not email) to say that you’re going to be in town and would he like to get together for drinks.

If you do want to follow through with this I would definitely include your brother. It wouldn’t be fair to drive a potential wedge in the relationship with his close friend if he isn’t ok with working around “it” if things didn’t work out with you and Peter. Also, if he is stoked at the idea he can “set you up” a lot better than you could alone.

To add to the long distance concerns…med school is very intense so he may not be up to the challenge of balancing an LDR right now and if he isn’t close to graduating then that reduces the chance he would go for this.

I think whoever touched on the point of LW building this up in her head is correct. Also, I’d just like to add that most people don’t realize just how intense medical school is, so if you’re looking for any attention or time from him should he even be interested, its unlikely to happen any time soon. And don’t sneak around your brother’s back. Thats childish and not right to do to him or the guy.

To mirror what Kate said above, I don’t really understand WHY you’ve decided to all of a sudden reach out to him. You didn’t give any reasons that touch on HIM – “He’s extremely intelligent, hardworking, fun, attractive, seems like my type, etc.” – In fact, you said absolutely nothing about him! It seems like when your sister casually mentioned him 2 years ago, you took that idea and ran with it. And, as Kate said above, you built him up in your head.

To me, I don’t get the impression from your letter that you’re even romantically interested in HIM…you’ve just decided you’re ready for a relationship and you scrolled through your mental file and plucked him out. That’s definitely NOT how you should approach the world of serious relationships…you need a reason to want to date someone other than “my sister once said we should go out 2 years ago.”

Why don’t you try concentrating more on dating with the aim of a serious relationship where you are? After all, Peter lives 9 hours away and hasn’t heard from you in 2 years. You’d have much better luck meeting someone where you are than trying to build a relationship from nothing, with someone you don’t seem all that interested in, who happens to be 9 hours away in medical school.

If you’re worried about encountering a bunch of dead-end dates, why don’t you fish from your social circle? Ask friends to set you up with someone, start going to more social gatherings, venture out on your own to things you’re interested in (concerts, book readings, exercise clubs, etc). You’re bound to eventually meet a guy who you have something in common with while you’re doing that!

In the LW’s defense, she did mention reasons she liked him in the original letter (I edited some stuff out for brevity). She wrote: “In my list of qualities I look for in a guy, he meets every one: he’s 32 (I’ve always seen myself with someone 6-8 years older), educated, goal-oriented, Catholic, good-looking, etc. I’ve always been attracted to him.”

Ok, well that does change some things! But I still agree that she’s built him up a bit in her head, and that she’d be better off to pursue dating in her immediate area…especially since they haven’t spoken in 2 years.

“I don’t really understand WHY you’ve decided to all of a sudden reach out to him.”>

Cuz she can’t have him! I’m sure she could find good looking, older Catholic dudes locally if she wanted to, but it’s all about the forbidden fruits! She can daydream about Peter and make him whatever she wants in her mind since he’s 9 hours away and in school, and they haven’t even seen each other in years.

I agree with other commenters that you are fixating on this guy because you don’t have any immediate options. You need a distraction and a crush, and Peter fills that void for you when you need a love interest to pine over. We’ve all been there. And honestly, I don’t think there’s anything wrong with casually shooting off an email and seeing if anything comes from it. My worry with you is that you’ve built this guy up so much (even picturing a relationship with him even though you haven’t seen him in years and he lives 9 hours away) that you would be waaaay too emotionally invested. I developed a long term crush once and basically ended up tied to my computer, hoping he would get on gchat, while he was just casually flirting with me but going about his life as normal. Nothing more came of it, and while that would have been fine if I had just been looking at it as a fun flirtation with a cute penpal, I was bummed because I had halfway convinced myself that we would be dating someday.

Another thing: having an awkward conversation with your brother isn’t really the worst thing. That said, I think if you’re serious about this, it would be less awkward to just tell him you think Peter’s cute, as opposed to getting a phone call from him asking why you’re suggestively emailing his friends. If you truly think there might be something there with this guy, you need to be willing to be a little embarrassed.

Ok, this one hits a little close home, haha. I’m currently talking obsessively to a guy who lives 16 hours away, in MY home state, with whom I was set up via facebook by a mutual acquaintance. The only reason I even considered it was because I do plan to move back there next year sometime, so I know that if we do start something it won’t always be long distance.

Is it crazy? Probably. Am I going to stop? Hell no. He’s amazing.

So, LW, there are some things you should think about. You say you have no plans to move home. Does Peter plan to stay in your home state? Do you even know? How far along is he in medical school- how much longer does he have? He might not be dating anyone, but is he otherwise involved? Is he even single and/or looking? Can you afford to go home to visit him frequently? Med school is a HUGE time commitment, so I doubt he’ll be able to come see you often. When was the last time you actually talked to Peter? Is it possible he’s changed significantly from the last time you saw him? Do you actually *like* him as a person, or just his “resume” of age, career, religion, etc.?

This is the kind of stuff you can put off thinking about for months when you just start dating/hooking up with someone who lives close to you. But when you throw distance into the mix it magnifies every little issue x10, at least. Not to mention the whole “my brother’s best friend” side of things, which works well in romance novels and not so well in real life. Any idea how he’ll react? Do you really want a relationship with this guy, or do you just want to satisfy your curiosity?

My crush/bff from freshman year of college happened to be in town…we met up…magic? He never knew I liked him.

We have never kissed, but now we are emailing & talking on the phone & he just sent me a song he wrote for me freshman year. I can’t even listen to it yet. Just the first couple lines of his email already had me in tears?

& he is in law school & lives states away from me….so….why did I do this to myself again? I cannot tell if any of this is really in the present, or if we’re living out our past fantasies. Anyway, I hate LDRs & we’re dating other people for now.

Long, tangent aside —- LW, I say joke to your brother, “When’s Peter going to be in town next? Last time I saw him he was looking cuuu–uuu-uuute.”

Gently remind him that you are a woman & may have an interest in his friend.

Hang out with Peter, ask him to walk you to your car/ask to walk him to his car/seize a moment when you’re alone & say, “Can we kiss? I like you & I’m curious if we might actually have chemistry.”

I don’t see how or why your dating troubles would suddenly go away just by starting a relationship with someone 9 hours away. You’re the common factor in your dating so look at yourself to see why dating isn’t working. Until you figure out what’s going wrong there’s probably little hope that anything would work with Peter even if you did live in the same city.

My second thought is that all the traits you listed are somewhat superficial. I know that age and religion are intrinsic but they don’t say anything about basic personality and compatibility with you. Even values vary drastically among people of the same religion. Just walk into any Catholic church and you will see families with one or two half grown children (birth control) and many less families with five or more children (no birth control.) You will see people in the prolife movement but you also see statistics that say over half of all Catholics are prochoice.

You remind me of the mother of a guy I dated. She always wanted to marry a black haired, Catholic, farmer. Well, his dad was all of that and also a liar and cheat and his stream of affairs destroyed the marriage. I think you need to spend more time looking beneath the surface traits for the real personality that matches your own.

Truly it sounds like the LW is a little bored and the thought of Peter offers up a welcome distraction for her. But it is dangerous to have fantasy distract you from real possibilities. If Peter was everything she has always wanted it wouldn’t have taken her two years post suggestion from the sister to seriously consider him. Peter hasn’t changed in the last two years – the LW’s dating success in her own town has.

The main thing that strikes me as odd here is why not just talk to your brother about this? Do You two not get along or something? Wait, no. You even mention that this is your closest brother, so, what gives? Or would he simply NOT be happy about this? Many, many questions. Yes, something has seriously been left out of this letter.

The other curious thing is how dated it all feels. Desperately tracking down somebody’s email from a school directory is so all 1998. Are none of you on Facebook? The reason I ask is because Facebook would simply be a much easier way to approach somebody in a much more casual way. “Hey, I saw your post about __________ on my brother’s page, and realized I haven’t seen you in ages! How have you been?”

Obviously, though, all this happens AFTER you sort things out with your brother… Going behind his back seems very sneaky and suspicious. What are you trying to hide?

Ha! I was thinking the same thing. Aren’t they already facebook friends? That’s the first thing she should do, is friend-request him. LW, you could do that without first going through your brother. So if for whatever reason you don’t want to talk to him (your brother) about it first, just friend request the dude. That’s wayyyyy less stalker-like than tracking down an email address and emailing him. People friend request people they barely know – and even though often rarely actually communicate once the request is accepted. So that would be an easy way to get in contact with him. And who knows, maybe he’ll even shoot you a message to say hi when he accepts your friend request. And then voila, go forth and communicate.

The part that jumped out to me is that in the list of qualities she looks for in a man, she cites their age difference as exactly what she’s looking for. Really? Some guy you barely ever speak to, who lives 9 hours away, is perfect for you partially because he’s 32? I agree with others that the LW is putting this guy up on a pedestal because of some arbitrary list of qualities.

Oh, and it’s been shown that when doing speed dating, the list of qualities you claim to be looking for in a man don’t influence who you pick. If I remember correctly, if you’re asked the day after speed dating, your list will have changed so that it’s more aligned with the qualities of the men you chose, but if you’re asked again a month later, your list will have reverted back to your original one. (I read this in Blink, which I highly recommend.) So really, the idea of choosing a guy who you have no contact with based on your list of desired qualities is just about the worst way to choose a man.

My friend wanted to date my sister (a little bit different) and he asked me before he asked her out. His first communication to her via fb message was (after they met in person at a party of mine): “hey, how did the first day of school go?” She is a teacher. She answered, he asked her for coffee, more dates followed and now they are getting married next June.

Why don’t you friend him on FB first and then say hi that way? That’s my advice.

It sounds like you’ve put a lot onto a fantasy, and it should probably stay as fantasy. If you see again in passing, then great. If something were to work out, cool. But I think that emailing him because you have a crush is…. a little childish.

I would steer clear of emailing him. Why not just try friending him on FB and see if you actually have anything in common. It would be a lot less weird and more casual.

People change a lot in the course of two years, which means that you really don’t know him at all. I think what you are suggesting really has the potential to come off as strange and awkward more than it does to become a romantic relationship.

Yeah, if a guy tracked down my email from my company directory (thank goodness we don’t give that out to folks outside of the company) and cold emailed me for a date, my stalker-radar would be pinging. I’m sure that this guy’s would be sending signals too – even if you are his best friend’s sister.

Not to mention your brother. This is your closest brother. Why not talk to him? He could talk you up a bit. At least give the guy some warning so you don’t come off stalkerish and put the guy off. What if this guy is not interested in girls? Your brother would know, and it would save YOU some embarassment. Don’t play games – talk to your brother and play it straight.

I agree, I actually had this guy I went to highschool with friend request me on FB, and then as soon as that happened he got my phone number off of it, and then started to text me right away. This was a non-romantic situation, and was creepy enough! So I de-friended this kid, and then a year later he friend requested me again, and the same thing happened. I excepted the second request, because I forgot all about the first time until he did it again.

I also had a guy that I built WAYYY up in my head and I would sit around and devise plans to get in touch with him or to run into him, and get REALLY disappointed when it never worked. He was someone I casually dated when I was very young; I guess you could call it a “summer fling” that just…fizzled out. He was incredibly good-looking and the best kisser EVER, about 4 years older than me, in a band, and just… I dunno. I was in AWE of him. We fizzled out when I went back to college, then he got a girlfriend and I got a boyfriend, then I moved across the country, then he moved out of our hometown…. I kept him in the back of my head the WHOLE time. The more I dated losers, the more I thought this guy was truly THE ONE that got away, and I thought we would “end up” together someday, somehow. Fast forward 8 years and suddenly we’re living in the same town again, and he’s almost done with med school, and FINALLY we get to spend some real time together. (We had kept in touch via facebook, text, etc. all this time as friends but hadn’t seen each other in person for YEARS). The first time I saw him, he literally looked…smaller…than I had remembered. And not QUITE as cute. But not only that – while he had all of the qualities that I thought were important in a partner (more of the superficial stuff, like what the LW mentioned) – WE didn’t mesh well together. He is much more conservative than I am, politically, which I wouldn’t mind if he was able to RESPECTFULLY disagree with me. He also wants kids right away, whereas I’m not sure if I want them ever. And based on his political beliefes, I think that if we did have kids, we would have disagreements about how to raise them. And THESE are the things that matter.

My advice is to not email him randomly. The Facebook idea is a good one, but I’m thinking if you haven’t done that yet, there must be some reason (maybe he’s not on facebook?). I agree with the other LWs to wait and see if you can “run into” him over a holiday or something. Thanksgiving is not that far off. See how you 2 interact face to face.

Also, I think you should work on your “list” of qualities for a potential partner a little bit more. I went though some relationship hell and questioned for YEARS whether or not I even wanted to go through the hassle of dating EVER again. My therapist helped me work on a list – and soon after, I met my boyfriend , and he embodies all of THOSE qualities that I discovered were important, and we get along famously, and it’s actually the best and healthiest relationship I’ve ever been in.

So don’t fret, LW! I can see how, at age 25, you are ready to start dating someone seriously, perhaps someone that you’d consider “marriage material”… but if you narrow your focus to JUST this one guy, and compare all others to the image you’ve created of him in your head, I think you’re setting yourself up for disappointment.

The first is that you would go behind your brother’s back. What if he doesn’t approve and now you’ve started this fight between you and the brother you are closest to. Is that something you are really willing to risk?

Second, I don’t think Peter will be able to give you what you are looking for. I may be completely misreading here but it seems to me you want a boyfriend who is there, with you…who will hold your hand, go on dates with, spend the day in bed with, run boring errands with, etc. Peter is not going to be that guy. Peter is 9 hours away and I’m sure Peter is incredibly busy with medical school. I think it would probably be in your best interest to continue your search locally and don’t waste your time otherwise. It’s not easy finding someone you connect with and can build that relationship but you’ll just appreciate it that much more when it does happen.

LW, i reallly think that they only way your going to ever date this guy is through your brother. i mean, he is your brothers friend, not yours. i just cant imagine that if you tried to contact him outright (no matter the means of communication) it going to be weird when he says to your brother, “oh yea, your little sister emailed me/friended me on facebook, and she is totally talking with me now. nothing wierd, just messages about her life, and asking about mine. its totally out of the blue” and then your brother says something alone the lines of “shes emailing you? what? why?”. i just cant see that situation becoming good. its just going to be awkward.

also, LW, i would like to tell you that doctors are one of those professions that women SAY they want to date/marry, but actually hate it. i heard it on the radio once, they did a big discussion on it. dating a doctor is terrible. for the first years of it, they have almost no control of where they are moved to, and then after that whole thing, there are the endless hours and always being on call with a pager. i just wanna warn you that dating a doctor isn’t actually all amazing like its cracked up to be. good money, yes, but almost no time together. other professions were musicians and professional sports players… i cant remember the others, but it was a interesting talk. just an fyi for you! lol

One additional consideration: I work with doctors (although I’m not one myself), and most of them are married to other doctors. By and large, doctors date doctors. It’s such an intense, all-encompassing career that they are most comfortable with partners who are living it themselves. Which is not to say that Peter definitely won’t be interested, but it certainly counts against it.